A Tunable and Enantioselective Hetero-Diels-Alder Reaction Provides Access to Distinct Piperidinoyl Spirooxindoles
| Autor: | Kamal Kumar, Carsten Strohmann, Samydurai Jayakumar, Kathrin Louven |
|---|---|
| Rok vydání: | 2017 |
| Předmět: |
Magnesium salts
Natural product Chemistry Ligand 010405 organic chemistry Enantioselective synthesis chemistry.chemical_element General Chemistry General Medicine 010402 general chemistry 01 natural sciences Catalysis Cycloaddition 0104 chemical sciences chemistry.chemical_compound Dysprosium Organic chemistry Diels–Alder reaction |
| Zdroj: | Angewandte Chemie. 129:16161-16165 |
| ISSN: | 0044-8249 |
| Popis: | The active complexes of chiral N,N-oxide ligand with dysprosium and magnesium salts catalyze the hetero-Diels-Alder reaction between 2-aza-3-silyloxy-butadienes and alkylidene oxindoles to selectively form 3,3´- and 3,4´-piperidinoyl spirooxindoles respectively in very high yields and with excellent enantioselectivities. The exo-selective asymmetric cycloaddition successfully regaled the construction of sp3 rich and highly substituted natural product based spirooxindoles supporting many chiral centers including consecutive all-carbon-quaternary centers. |
| Databáze: | OpenAIRE |
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